1203608-46-1Relevant articles and documents
Toward safer processes for C-C biaryl bond construction: Catalytic direct C-H arylation and tin-free radical coupling in the synthesis of pyrazolophenanthridines
Hernandez, Susana,Moreno, Isabel,SanMartin, Raul,Gomez, German,Herrero, Maria Teresa,Dominguez, Esther
supporting information; experimental part, p. 434 - 441 (2010/03/30)
(Chemical Equation Presented) A series of pyrazolo[1,5-f]phenanthridine derivatives has been efficiently synthesized by a short, straightforward sequence. A tandem amine-exchange/heterocyclization of enaminones was successfully applied to the regioselective preparation of 1,5-diarylpyrazole intermediates with structure resemblance to relevant nonsteroidal anti-inflammatory drugs such as celecoxib or tepoxalin. The final key step, cyclization by intramolecular biaryl bond formation, was accomplished by two alternative methodologies: radical coupling and catalytic direct arylation via C-H activation. The scope and limitations of the two methodologies have been explored and their complementariness has been established. In addition, polymer-supported heterogeneous catalysts have been compared with homogeneous analogues. In the radical process, toxic tin derivatives have been avoided in order to employ environmentally safer protocols.